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A paradigm shift design of functional monomers for developing molecularly imprinted polymers

Li, Qianjin LU ; Ling, Baoping; Jiang, Lingdong LU and Ye, Lei LU (2018) In Chemical Engineering Journal 350. p.217-224
Abstract

Functional monomers play a key role in preparing molecularly imprinted polymers (MIPs) by forming complex with templates to create recognition sites in the polymers. In this paper, a new strategy was proposed to design functional monomers for efficient MIPs synthesis. This strategy dated from the investigations on previously developed MIPs. In propranolol imprinting process, methacrylic acid has always been used as a functional monomer, due to the efficient hydrogen bonding interactions between the carboxyl group in methacrylic acid and the 2-hydroxylethylamine group in propranolol. Given this, we assumed that a functional monomer having a 2-hydroxylethylamine moiety may be used to imprint carboxylic acid molecules e.g. naproxen. To... (More)

Functional monomers play a key role in preparing molecularly imprinted polymers (MIPs) by forming complex with templates to create recognition sites in the polymers. In this paper, a new strategy was proposed to design functional monomers for efficient MIPs synthesis. This strategy dated from the investigations on previously developed MIPs. In propranolol imprinting process, methacrylic acid has always been used as a functional monomer, due to the efficient hydrogen bonding interactions between the carboxyl group in methacrylic acid and the 2-hydroxylethylamine group in propranolol. Given this, we assumed that a functional monomer having a 2-hydroxylethylamine moiety may be used to imprint carboxylic acid molecules e.g. naproxen. To demonstrate this idea, a new monomer 2-hydroxy-3-(isopropylamino)propyl methacrylate (HIMA) was designed. Computation results, by means of density functional theory method, revealed that HIMA could form a stable complex with naproxen through hydrogen bonding interactions with the carboxylic acid group. HIMA was then used to synthesize naproxen-imprinted polymers via precipitation polymerization. Binding experiments showed that all the MIPs could selectively recognize naproxen, confirming the feasibility of our paradigm shift in functional monomer design. The new functional monomer HIMA is a promising ligand that may be used to imprint other molecules having carboxylic acid or phosphoric acid groups. The paradigm shift in this study thereby opens a new avenue to design functional monomers for developing MIPs.

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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
Carboxylic acid, Functional monomer, Molecularly imprinted polymer, Naproxen, Propranolol
in
Chemical Engineering Journal
volume
350
pages
8 pages
publisher
Elsevier
external identifiers
  • scopus:85047815830
ISSN
1385-8947
DOI
language
English
LU publication?
yes
id
ddbe8f20-053c-4398-978c-da6650796758
date added to LUP
2018-06-11 10:11:19
date last changed
2018-06-11 10:11:19
@article{ddbe8f20-053c-4398-978c-da6650796758,
  abstract     = {<p>Functional monomers play a key role in preparing molecularly imprinted polymers (MIPs) by forming complex with templates to create recognition sites in the polymers. In this paper, a new strategy was proposed to design functional monomers for efficient MIPs synthesis. This strategy dated from the investigations on previously developed MIPs. In propranolol imprinting process, methacrylic acid has always been used as a functional monomer, due to the efficient hydrogen bonding interactions between the carboxyl group in methacrylic acid and the 2-hydroxylethylamine group in propranolol. Given this, we assumed that a functional monomer having a 2-hydroxylethylamine moiety may be used to imprint carboxylic acid molecules e.g. naproxen. To demonstrate this idea, a new monomer 2-hydroxy-3-(isopropylamino)propyl methacrylate (HIMA) was designed. Computation results, by means of density functional theory method, revealed that HIMA could form a stable complex with naproxen through hydrogen bonding interactions with the carboxylic acid group. HIMA was then used to synthesize naproxen-imprinted polymers via precipitation polymerization. Binding experiments showed that all the MIPs could selectively recognize naproxen, confirming the feasibility of our paradigm shift in functional monomer design. The new functional monomer HIMA is a promising ligand that may be used to imprint other molecules having carboxylic acid or phosphoric acid groups. The paradigm shift in this study thereby opens a new avenue to design functional monomers for developing MIPs.</p>},
  author       = {Li, Qianjin and Ling, Baoping and Jiang, Lingdong and Ye, Lei},
  issn         = {1385-8947},
  keyword      = {Carboxylic acid,Functional monomer,Molecularly imprinted polymer,Naproxen,Propranolol},
  language     = {eng},
  month        = {10},
  pages        = {217--224},
  publisher    = {Elsevier},
  series       = {Chemical Engineering Journal},
  title        = {A paradigm shift design of functional monomers for developing molecularly imprinted polymers},
  url          = {http://dx.doi.org/},
  volume       = {350},
  year         = {2018},
}